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Chester VT Real Estate

Located in Windsor County, Chester is a wonderful New England town reminiscent of a bygone era. With architecture pre-dating the civil war, Chester is rich in history and beauty. Although historic, the quaint town is thriving with its unique markets, galleries, and restaurants that offer much to do. The town is also conveniently located close to Okemo Mountain and Mount Snow for those who enjoy outdoor recreation as well as within driving distance to Manchester, VT

Search the latest real estate in Chester, VT with Maple Sweet Real Estate. Find the right property for you from a variety of listings. To save your favorites, register with us and you can get email notifications when similar properties are posted. Already have an account with us? Log in here.

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326 Goodrich Road Chester VT 05143

Chester, VT326 Goodrich Road

Price$6,000,000The price has recently decreased

MLS Number 4963698

  • Commercial
  • Square Feet 1,760
  • Year Built 2019
  • Acreage 25.99
  • PricePerSqFt 3409.09

This is a first class stone quarry operation which pumps out a beautiful stream of high grade gneiss stone, so indispensable for the building trades in constructing patios, steps, walls, chimneys, and every place beautifully ad naturally colored building stones are needed. The next owner of this business will of course be buying a highly profitable and proven going concern. However, the next owner will have seen the monumental opportunity in the $168,000,000, in unmined, and yet very minable stone as attested to by the attached professionally prepared geological report. Complete with $1.5 M worth of meticulously maintained equipment and an immaculate stone cutting shop, this offering spells opportunity writ large. While the Owner believes the next owner will be someone already in the industry, and he may be correct, I also believe that it could be anyone who sees the brilliance of buying assets for pennies on the currently shrinking and inflated dollar along with a proven and successful method for extracting same. But what do I know? I'm just a Realtor. But an entrepreurial MBA Realtor nonetheless who will be happy to show you this opportunity in person.

Listed by Lawrence Zupan of EXP Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.22% last updated on 2023-11-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

46 Vermont Route 103 S Chester VT 05143

Chester, VT46 Vermont Route 103 S

Price$699,000The price has recently decreased

MLS Number 4965884

  • Commercial
  • Year Built 1966
  • Square Feet 1,316
  • Acreage 0.59
  • Area Commercial Zoning

The Country Girl Diner - a genuine Silk City Silver dining car (serial #178). The diner; recently featured in Yankee magazine "20 Diners Worth The Drive" issue, offers a rich history dating back to 1944 when it was built in Patterson, New Jersey. Located in the charming town of Chester, Vermont, this iconic diner has been a beloved part of the community since 1966. While a kitchen has been thoughtfully added to the rear of the diner to cater to modern needs, The Country Girl Diner still exudes a nostalgic ambiance that sets it apart from contemporary eateries. The unique blend of history and culinary delights makes it a truly one-of-a-kind destination. Don't miss the opportunity to own and cherish this piece of living history. The owners have updated and maintained this beautiful structure with love and care over the years and are ready to hand it over to someone new who has a passion for the restaurant industry. Whether you're a diner enthusiast, a lover of tradition, or seeking a business venture with character, The Country Girl Diner awaits you!

Listed by Craig Ruggless and Kate Barry of EXP Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.22% last updated on 2023-11-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

252 Davidson Hill Road Chester VT 05143

Chester, VT252 Davidson Hill Road

Price$680,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4975126

  • Residential Single Family
  • Bathroom 3
  • Square Feet 4,070
  • Bedrooms 3
  • Construction Existing

This fantastic and spacious modern farmhouse, sitting on 11 acres, is perfect for anyone who loves to entertain, with plenty of room for friends and family. New flooring and paint throughout. The first floor is open and bright with white shiplap walls and bar, laundry room, and updated half bath with marble vanity and farmhouse sink. The kitchen has granite counters, stainless steel appliances, wine fridge, large island, and walk in pantry for extra storage. The radiant heat, HearthStone wood stove, and Lifebreath air system make this home efficient. The second floor has cathedral ceilings, full bath and three bedrooms; one with a loft. The large primary suite with window seat is perfect for reading. The barn doors open to the primary bath with jetted tub and oversized shower. The primary also has a large walk in closet with custom built-ins. The bonus room is perfect for a home gym. The basement with walk out can be finished for added living space. The additional 30X40 building would make a great workshop or studio. Enjoy the spectacular views from the expansive farmers wrap around porch. The deck offers extra outdoor space. This wonderful private property provides garden space, fenced in yard, chicken coop, and space for animals. With its ideal location to amenities and Okemo Mountain Resort, this modern farmhouse is a must see. Delayed showings until 10/28/23 from 10AM-1PM by appointment.

Listed by Cassandra Ehrlich of BHG Masiello Brattleboro

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.22% last updated on 2023-11-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

157 Murdock Road Chester VT 05143

Chester, VT157 Murdock Road

Price$665,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4954753

  • Residential Single Family
  • Construction New Construction
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,051

This 3-bedroom house on 30+/- acres near Okemo, with a blend of artistry and environmental features, is a dream home in progress. The use of high-quality materials, sustainable construction, and off-grid origins make it unique. This home is so close to being finished, the new owner will get to personalize it and make it their very own. The house is ready to occupy so you could jump right in and enjoy VT living! The house, now grid-connected, boasts a Kohler generator, solar panels, cedar siding, and a standing seam roof. Inside, eco-friendly quartz countertops, an Italian LaNordica wood cook stove, and locally milled oak floors showcase the commitment to sustainability. The open main level includes a bedroom, office, full bath, and laundry. Upstairs houses two bedrooms, while the lower level walkout features a Morso wood stove and unfinished rooms. Additionally, the property includes an off-grid cottage with a kitchen, wood stove, solar panels, and loft. Priced for completion, it awaits a new owner to bring this masterpiece to life.

Listed by Katherine Burns and Joseph Karl of William Raveis Vermont Properties

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.22% last updated on 2023-11-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

656 Main Street Chester VT 05143

Chester, VT656 Main Street

Price$625,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4963158

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Square Feet 3,040
  • Bedrooms 3

Presenting the Walter Austin House, a 3+ bedroom, 2.5 bath Queen Anne style Victorian on .37 +/- acres in the Chester Village. This grand home has many period features and combines qualities from the Gilded Age with a more contemporary lifestyle. The first floor features a tiled mudroom, elegant foyer and spacious living room with an attractive gas marble fireplace. Pocket doors open from the living room to the large formal dining room. The efficient, classically styled kitchen has a breakfast bar, Corian countertops and accented glass-paned cabinets. The spacious great room with cathedral ceilings, skylights and radiant flooring has a palladium-crowned triptych window that showcases a pastoral view which delights year round. The second floor features 3 bedrooms and continues the elegance of the foyer with crown moldings and stained glass windows. A spacious bathroom with a clawfoot soaking tub and large tiled shower is located across the hall from the convenient laundry room with half bath. The finished third floor Aerie offers two cozy rooms for office and study or guest overflow. The grounds are lovely and feature a side deck with an awning off the great room, a private courtyard and a luxurious relaxing swim spa! In addition to the 1 car garage, a two story post & beam barn provides additional garage and workshop space with a second floor rec room or private office. Proximity to skiing, Chester Village Green and town rec area make this a wonderful primary or vacation home

Listed by Geralyn Donohue of Engel & Volkers Okemo

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.22% last updated on 2023-11-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

665 Route 10 Chester VT 05143

Chester, VT665 Route 10

Price$574,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4965285

  • Residential Single Family
  • Construction Existing
  • Bedrooms 7
  • Bathroom 9
  • Square Feet 5,482

Ready for a life change? A farmhouse in Vermont is waiting for you! Once featured in Country Inns of New England, this property could be yours! The prior owner once operated a successful 24-seat restaurant and an inn. There are five guest rooms - 3 with their own bathrooms and 2 that share a bath, plus 2 double-room suites with their own bathrooms, as well as a four-room owner's suite. One guest suite is undergoing renovations. The stone-floored "Speak Easy" tavern is a great space for conversations and fun. The barn has endless potential for business, guests, yoga, events, or even animals. Set up the white tent on the level lawn next to the barn and decorate the bridge for weddings at the pond (recently dredged and ready for swimming or Winter skating). The small barn is perfect for many uses, smoking meats, or raising chickens. There is even an old milk house for a farm stand! Located conveniently to I91, Okemo Mountain (only a few minutes drive), several other ski resorts, the villages of Chester, Weston and Cavendish. There is much to love about this antique farmhouse property...start your business, your farm, or just enjoy it yourself as a retreat or workplace. Ten acres, a pond, barns, and a large farmhouse. More photos and information will be added as work is being completed. An extensive list of the current owners' improvements and is available and being updated as work is done. New photos will continue to be posted as well. This property is easy to view.

Listed by Tyleen Murray of Kelley Real Estate,Inc.

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

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Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.22% last updated on 2023-11-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

418 Davidson Hill Road Chester VT 05143

Chester, VT418 Davidson Hill Road

Price$549,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4964887

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,458

This beautiful log home is perched upon a hill providing great views and an on top of the world feeling. The long range views can be appreciated outside on the wrap around deck or inside through the large windows in the living space. This property features a wonderfully sculpted eye catching stone fireplace that is sure to set the mood on a snowy evening or late summer night. The property also features a pine board interior with the classic Vermont log cabin look and feel as well as a wood stove to add to the ambiance. The primary bedroom features a large walk in closet with a 3/4 bathroom attached as well as a balcony overlooking the back woods. All this plus a garage in the basement to fit all of your winter or summer toys and, it's also only about 20 minutes to Okemo Resort, 30 minutes to Magic Mountain Resort and 18 minutes to the Weathersfield hiking trail on Ascutney Mountain.

Listed by Thaddeus Abare of Barrett and Valley Associates Inc.

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.22% last updated on 2023-11-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1709 Potash Brook Road Chester VT 05143

Chester, VT1709 Potash Brook Road

Price$499,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4970124

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,688

This spacious custom 4 bed,3 bath home sits on 7 acres of land near the end of a dead-end country road and is minutes from the Village of Chester. Built in 2008, this home has ample storage, a large laundry room with a ¾ bath and a roomy primary suite with a custom tile shower, a Japanese soaking tub, and a private deck. The main level of the house has a large living room with brand-new flooring, a wood stove and stone hearth and sits adjacent to the gourmet kitchen featuring a commercial hood over the “Blue Star” 6 burner gas range and pot-filler faucet. The large open plan main level opens to the covered deck and 12 x 22 blue stone patio. On the same level is a large den/office which could be used as a 2nd living room, library or guest bedroom. While the living areas are spacious and comfortable the wrap-around porch is where you will want to spend all your time. This home was built in a controlled environment using 2 x 6 construction with plywood (not composite), copper piping, 10” basement concrete walls & radiant heat in the basement floor. The decking is low-maintenance Trex material and the siding is a high-quality vinyl. The grounds include several perennial gardens and a 6' deep pond. The basement level is just waiting for your imagination. Skiers, snowboarders, snowmobilers, or just an out door enthusiast be aware, this is an ideal property and location; less than 30 minutes to 3 major ski resorts, close to VAST snowmobile trail, and a short drive to the Chester!!

Listed by Daire Gibney of Barrett and Valley Associates Inc.

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

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Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.22% last updated on 2023-11-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

134 Gold River Extension Chester VT 05143

Chester, VT134 Gold River Extension

Price$425,000The price has recently decreased

MLS Number 4952929

  • Commercial
  • Square Feet 6,656
  • Acreage 2.49
  • PricePerSqFt 63.85

Rare opportunity with commercial/industrial zoning. 2.49 acres that is fully permitted. Property can be used as one business spot, or share the office building with another business. Currently there are 3 buildings onsite to include: 1792 sq ft office building; 3364 sq ft garage building with heat, loading dock, office, and rail siding; plus an additional 1500 sq ft storage building. Property includes an owned rail siding for direct shipment possibilities. Highway access is on Route 11 East, 3/10's of a mile from Route 103, and 9 miles to Route 91, exit 6. Office building has center entry and two administration wings, could be used by two or more businesses. Fiber-optic internet is on site. Garage building is currently used for service of trucking and excavation equipment and includes office area. This building has loading dock and direct access to rail siding. Common rail siding to be maintained for all. Currently there is a tenant in the office building. Video attached to the MLS.

Listed by Andy Paluch of TPW Real Estate

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.22% last updated on 2023-11-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

117 South Main Street Chester VT 05143

Chester, VT117 South Main Street

Price$399,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4956139

  • Multifamily
  • Units 3
  • Bathroom 3
  • Acreage 0.75
  • Square Feet 2,008

Opportunity awaits! This three-unit property has been very well maintained and is fully rented with long term tenants. This investment features an in-town location within walking distance to shopping, restaurants and local conveniences. This property also includes additional unfinished square footage in the barn, currently used for storage, with great potential for new ideas. Even the basement is impressive. The outside of this home has been freshly painted as of 6/6/2023. All apartments are in good shape and fully applianced.

Listed by Thaddeus Abare of Barrett and Valley Associates Inc.

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

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Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.22% last updated on 2023-11-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

49 Putnam Hill Road Chester VT 05143

Chester, VT49 Putnam Hill Road

Price$399,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4973364

  • Land
  • Acreage 3.2
  • PricePerSqFt 124687.5
  • Zoning Res 20

The heavy lifting has been done on this 3.2 acre+/- parcel in the Putnam Hill neighborhood overlooking the village of Chester. A nicely sited driveway leads to the building site with foundation, framing, installed windows and solid wood doors and wide pine flooring on site for 2.5 levels of above ground living space. 200 Amp power is in place as well as a 5 bedroom septic system and drilled well/pressure tank. Designed for a total of 4,500 sf with 5 bedrooms and 4 baths plus a full 1800 sf walk out basement that could be finished as well. Owner built by experienced master tradesman. Views of the surrounding Green Mountains and within walking distance to Chester Village. No drive-bys please. Private driveway. Please note adjoining property also listed as mls # 4972814.

Listed by Geralyn Donohue of Engel & Volkers Okemo

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.22% last updated on 2023-11-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

49 Putnam Hill Road Chester VT 05143

Chester, VT49 Putnam Hill Road

Price$399,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4972797

  • Residential Single Family
  • Construction New Construction
  • Bedrooms 5
  • Bathroom 4
  • Acreage 3.21

Located in the neighborhood of Putnam Hill in Chester, this newly constructed dormered 2.5 story 5 bedroom, 4 bath home on 3.2+/- acres has been framed and is utility ready with septic, well, electric in place. The first floor space features a Great Room with 16' ceilings at its highest points, large kitchen with work area and plenty of cabinet space, a separate dining room for large gatherings, a formal living room and full bath which could also function as a first floor bedroom. The second floor is designed for 4 bedrooms and 2 full baths and the third floor has flex space with four large dormers and beautiful views. This thoughtfully designed home includes a walkout basement with 9' ceilings and intentional framing to include large windows. Solid wood doors are on site along with 10” wide plank pine flooring, furnace and misc. materials. This home was built by a Master tradesman with years of experience. The architectural framing is quite remarkable as is the desirable location of Chester VT with short drives to various ski mountains.

Listed by Geralyn Donohue of Engel & Volkers Okemo

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 7.22% last updated on 2023-11-30

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Broker Reciprocity 

Copyright 2023 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated December 2, 2023 9:39 AM EST

 

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